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Well , it depends on how did u configured your outlook. which accoutn did u configurd, there are options if you allowed ur outlook to save emails into your computer hardesk and not save any copy on mail server then u dont have your emails back, however if u didnt choose the option then u will be able to retrive back your emails..
You cannot switch file systems and keep the data, you can however backup your data and reformat your hd, then proceed to copy from the backup media to the reinstalled OS. there are many tools to do both task, I would recommend download a linux live cd and backup to your external drive from there, then just reinstall windows and format your drive with an NTFS partition. I hope this helps.
Try changing the boot sequence in your CMOS setup, set your Main hard drive(I think it's IDE 0) and the rest is up to you whethere you will set the CD-ROM or the external HDD as the 2nd boot device. Once the computer starts just press DEL(most generic computers but for brand specific check the manual on how to access it) to enter the CMOS Setup.
if you can find or purchase another cable adapter just replace it. not worth fixing and might cause your external hard drive to crash if you get to fix the cable wrongly and will be spending more and losing both hard drive and cable